Anthraquinone dyes for wool



United States Patent '0 Patented Nov. 1, 1955 to form the correspondingacid which'is reacted with the ANTI-IRAQUINONE DYES FOR WOOL No Drawing.Application December 20, 1950, 10

bromanine acid.

The following example discloses a preferred embodiment of the invention,but it will be understood that variations and modifications may be madewithin the scope of the claims.

Example In a suitable vessel equipped with a stirrer was placed 21.8parts by weight N-(5-amino-2-methylbenzyl)succinimide, 200.0 partssodium hydroxide solution,

Senal 201867 by weight. The mixture was heated until solution was 2Claims. (Cl. 260-372) achieved. It was cooled and sufficient dilutehydrochloric acid was added to cause complete precipitation; a largeexcess was avoided. The mixture was filtered and the This inventionrelates to new and valuable dyestufis of the anthraquinone seriesyielding blue shades upon dyeing wool.

We have discovered a new group of dyestuffs having the following generalformula:

cake was mometer charged washed neutral. The cake was charged into asuitable vessel equipped with a stirrer, heater, therand refluxcondenser. Into this vessel was 24.3 parts sodiuml-amino-4-bromo-anthraquinone-Z-sulfonate, 26.5 parts of sodiumcarbonate, 2.0 parts cuprous chloride and 600.0 parts water. Themixstirred at 80 C. for sixteen hours. Then was added slowly 200.0 partssodium chloride solution and the mixture was allowed to cool to roomtemperature. The material which settled out was isolated by It may befurther purified by the usual techniques (such as precipitation fromaqueous basic solution by the addition of salt or precipitation fromsolution by O NH: 20

SO3H ture was O NH R R1 filtration.

wherein R is selected from the group consisting of hydrogen, halogen(chlorine, bromine), hydroxy, lower alkyl (methyl, ethyl, propyl,butyl), lower alkoxy (methoxy, ethoxy, propoxy, butoxy), carboxylic andsulfonic acid having one free carboxy group.

In general, these compounds are prepared by reacting1-amino-4-bromo-anthaquinone-2-sulfonate, so called bromamine acid, withan aromatic amine having an acylated aminomethyl group. The amines areprepared by reduction and hydrolysis of the nitro compounds disclosed inU. S. patent application Serial No. 136,166 to Saul R. Buc, filedDecember 30, 1949, now Patent No. 2,652,403. These compounds have theformula:

the addition of acid). monium salt for dyeing. The dyeings on wool wereattractive greenish-blue shades and showed excellent properties,especially to light. sented as follows:

It may be converted to the am- The reaction may be repre- The presentapplication is a continuation in part of our R O co-pending applicationSerial No. 132,397, filed December ll 10, 1949, now abandoned. NO Weclaim:

- 1. New dyestuifs of the general formula:

CI 0 NHZ u 1 0 SO3H wherein R is hydrogen, halogen, hydroxy, loweralkyl, lower alkoxy, or carboxylic and sulfonic acid group; and Rwherein Z represents acyclic or alicyclic hydrocarbon R radicalsnecessary to complete a cyclocarboimide ring, as l for example:

NOz R2 0 wherein R is selected from the group consisting of hy- /C CH2 6drogen, halogen, hydroxy, lower alkyl, lower alkoxy, -CH2N I 5carboxylic and sulfonic acid groups; wherein R is se- GH: lected fromthe group consisting of hydrogen and the N(2-methyl-5-nitrobenzl)succiuirnide Upon reduction this is converted to the corresponding aminocompound. Upon hydrolysis the ring is opened group R and wherein R hasthe formula:

oHlNHtllx wherein X is the residue of an aliphatic dicarboxylic acidhaving one free carboxy group.

3 r 4 2. A new dyestufi of the formula: References Cited in the file ofthis patent 1 UNITED STATES PATENTS 5033 1,946,829 Bayer Feb. 13, 1934 52,245,780 Heinrich June 17, 1941 2,533,178 Randall Dec. 5, 1950

1. NEW DYESTUFFS OF THE GENERAL FORMULA: